[3] Hamilton played his first tournament at the 1884 Irish Championships where he reached the quarter finals stage, before losing to Herbert Knox McKay.

This made him one of the favorites for the 1889 Wimbledon title but he suffered a five set defeat in the semifinal against Harry S. Barlow.

[4] He won the Gentlemen's Singles title at the 1890 Wimbledon Championships, defeating William Renshaw in five sets, and becoming the first Irish player to win the tournament.

Three brothers all excelled at sports; William Drummond Hamilton represented Ireland at cricket and tennis, Francis Cole Lowry Hamilton played cricket for Ireland and Blayney Hamilton represented Ireland at cricket and badminton.

[9][10] He died in Sydenham House, Dundrum, Dublin, on 27 September 1943 at the age of 78.